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I wanna get so deep into the deep web, that even Spider-Man is going to be jealous of how much web I have!

”

–Jackieboy Man, Jackieboy Man Returns

Brave, bubbly, independent and compassionate, he never hesitates to help someone in need and, in fact, relishes the thrill of the chase and the save. There are times that he can be clumsy, dropping or fumbling with his tools, which can make him seem unqualified for his job, but he's intelligent and has a great heart.

Jackieboy Man is loyal, honorable, and optimistic, always ready with a word of advice for his viewers. He's incredibly proud of his successes, usually sings and dances to celebrate, and is never one to back down from a fight, though he can be easily frightened if he's blindsided or ambushed. Impatient and impulsive, he sometimes forgets the necessary tools he needs for his mission or rushes off into danger without fully listening to the rules.

He tends to take most things at face value, trusting what he sees over what he's told, though he does have a vivid imagination. He has a keen sense of competition with other heroes, particularly Spiderman, and wants to prove his worth, often becoming snarky if he thinks he's being disrespected. His powers include x-ray vision, keen hearing, superior agility, and tentative hacking/coding skills, but his tendency to forget things and resulting need to double back and recheck his work can stand in his way.

Very little is known about Jackieboy Man's personal life: Jack wished Jackieboy Man a happy birthday on July 10th, 2016. Apparently he has poor eyesight outside of his x-ray vision and owns a pair of "Superhero glasses" that he needs to see when he is unmasked and even when he is masked if he's attempting to decipher code. He is also an enemy of Antisepticeye. Some believe that he is part of the LGBTQ+ community because of his playthrough of South Park: The Fractured But Whole, but Jack has confirmed that he dressed in Jackieboy's costume simply because it was a superhero game and that Jackieboy's appearance in that playthrough is not considered canon.

Jackieboy Man's first appearance was on October 25th, 2015 in the video "SPIDERMAN STEALS ALL YOUR STUFF" from the game Very Organised Thief. Though he is wearing a spiderman outfit, in the intro he clearly states that he is Jackieboy Man.

On July 10th, 2016, his second appearance was in the video "JACKIEBOY MAN RETURNS | Welcome To The Game #2", where Jack called upon him to hack the Deep Web because Jack had been scared by the previous run-through of the game.

On September 26th, 2016, he made his third appearance in the video “THE SCARIEST FUN! | Richies Plank Experience VR (HTC Vive Virtual Reality)” when he allowed Jack to experience flight and put out fires around the city.

On October 18th, 2016 he appeared in the video "Cool Patrol" by Ninja Sex Party. It started were he was supposedly just a nerdy boy being bullied by a group of males but was helped out by a super hero Danny Sexbang and his ninja friend. After a song and dance-number he was given his iconic red suit (this is while showing off his new found powers and confidence.) Sadly in the end he lost his fight by the bullies and became determined to never lose again. (At least that was said from the fans).

After nearly a year long absence, Jackieboy Man was heavily seen in Parts 2 - 13 of South Park: The Fractured But Whole series from October 20th, 2017 until November 27th, 2017. Jack was insisting that a superhero game required a superhero player. Jackieboy Man came out to dominate the opposing superheros and villains during the fighting portions of the game series. Unfortunately, Jack later confirmed that the let’s play was not canon for Jackieboy Man’s lore, saying he was just “dressing up as him for a joke”, meaning the superhero, as of August 2018, has not been seen in over two years.